EA006153B1 - СОЕДИНЕНИЯ ПИРРОЛО[2,3-d]ПИРИМИДИНА В КАЧЕСТВЕ ИММУНОДЕПРЕССАНТОВ - Google Patents

СОЕДИНЕНИЯ ПИРРОЛО[2,3-d]ПИРИМИДИНА В КАЧЕСТВЕ ИММУНОДЕПРЕССАНТОВ Download PDF

Info

Publication number: EA006153B1
Authority: EA; Eurasian Patent Office
Prior art keywords: methyl; pyrrolo; amino; pyrimidin; alkyl
Prior art date: 2000-06-26

Application number

EA200201096A

Other languages

English (en)

Russian (ru)

Other versions

EA200201096A1 (ru

Inventor

Тодд Эндрю Блуменкопф

Марк Эдвард Флэнэган

Майкл Джон Манчхоф

Original Assignee

Пфайзер Продактс Инк.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-06-26

Filing date

2001-06-05

Publication date

2005-10-27

2001-06-05 Application filed by Пфайзер Продактс Инк. filed Critical Пфайзер Продактс Инк.

2003-04-24 Publication of EA200201096A1 publication Critical patent/EA200201096A1/ru

2005-10-27 Publication of EA006153B1 publication Critical patent/EA006153B1/ru

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239000003018 immunosuppressive agent Substances 0.000 title description 2
229940125721 immunosuppressive agent Drugs 0.000 title 1
150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 134
102000001253 Protein Kinase Human genes 0.000 claims abstract description 8
108060006633 protein kinase Proteins 0.000 claims abstract description 8
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 383
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 294
-1 hydroxy, amino Chemical group 0.000 claims description 167
150000001412 amines Chemical class 0.000 claims description 104
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 90
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 56
238000000034 method Methods 0.000 claims description 39
150000003839 salts Chemical class 0.000 claims description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 15
125000001072 heteroaryl group Chemical group 0.000 claims description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 14
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 13
241000124008 Mammalia Species 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 10
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 9
108091000080 Phosphotransferase Proteins 0.000 claims description 9
125000004442 acylamino group Chemical group 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
208000035475 disorder Diseases 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
102000020233 phosphotransferase Human genes 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052805 deuterium Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
208000023275 Autoimmune disease Diseases 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
208000024827 Alzheimer disease Diseases 0.000 claims description 5
206010009900 Colitis ulcerative Diseases 0.000 claims description 5
208000011231 Crohn disease Diseases 0.000 claims description 5
206010012438 Dermatitis atopic Diseases 0.000 claims description 5
206010028980 Neoplasm Diseases 0.000 claims description 5
201000004681 Psoriasis Diseases 0.000 claims description 5
206010052779 Transplant rejections Diseases 0.000 claims description 5
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
229940121363 anti-inflammatory agent Drugs 0.000 claims description 5
239000002260 anti-inflammatory agent Substances 0.000 claims description 5
201000008937 atopic dermatitis Diseases 0.000 claims description 5
201000011510 cancer Diseases 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
210000000987 immune system Anatomy 0.000 claims description 5
208000032839 leukemia Diseases 0.000 claims description 5
206010025135 lupus erythematosus Diseases 0.000 claims description 5
201000006417 multiple sclerosis Diseases 0.000 claims description 5
210000000056 organ Anatomy 0.000 claims description 5
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 5
238000002689 xenotransplantation Methods 0.000 claims description 5
241000282412 Homo Species 0.000 claims description 4
208000024799 Thyroid disease Diseases 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
230000001363 autoimmune Effects 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
206010012601 diabetes mellitus Diseases 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
230000005764 inhibitory process Effects 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclo-pentanone Natural products O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 claims description 3
RHSBTQFWHDRNPH-UHFFFAOYSA-N n-(4-methylsulfonylphenyl)piperidine-1-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC(=O)N1CCCCC1 RHSBTQFWHDRNPH-UHFFFAOYSA-N 0.000 claims description 3
GHYWHYHXKQASKQ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)piperidine-1-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC(=O)N1CCCCC1 GHYWHYHXKQASKQ-UHFFFAOYSA-N 0.000 claims description 3
125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 2
HHNBSQGOZVNGPL-UHFFFAOYSA-N N-(1,3-thiazol-2-yl)piperidine-1-carboxamide Chemical compound S1C(=NC=C1)NC(=O)N1CCCCC1 HHNBSQGOZVNGPL-UHFFFAOYSA-N 0.000 claims description 2
CBXZLRVTULBFMR-UHFFFAOYSA-N O1N=C(C=C1)NC(=O)N1CCCCC1 Chemical compound O1N=C(C=C1)NC(=O)N1CCCCC1 CBXZLRVTULBFMR-UHFFFAOYSA-N 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
MRSMTDQHCJAKSB-UHFFFAOYSA-N n-(4-cyanophenyl)piperidine-1-carboxamide Chemical compound C1CCCCN1C(=O)NC1=CC=C(C#N)C=C1 MRSMTDQHCJAKSB-UHFFFAOYSA-N 0.000 claims description 2
HGOYOHNILBYFFX-UHFFFAOYSA-N n-(4-nitrophenyl)piperidine-1-carboxamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)N1CCCCC1 HGOYOHNILBYFFX-UHFFFAOYSA-N 0.000 claims description 2
JPWQXLMZEXLCHO-UHFFFAOYSA-N n-[4-(methylsulfamoyl)phenyl]piperidine-1-carboxamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1NC(=O)N1CCCCC1 JPWQXLMZEXLCHO-UHFFFAOYSA-N 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000005257 alkyl acyl group Chemical group 0.000 claims 6
125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims 1
125000000266 alpha-aminoacyl group Chemical group 0.000 claims 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
210000004907 gland Anatomy 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 3
102000006500 Janus Kinase 3 Human genes 0.000 abstract 1
108010019421 Janus Kinase 3 Proteins 0.000 abstract 1
DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 45
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
239000000203 mixture Substances 0.000 description 25
239000011541 reaction mixture Substances 0.000 description 25
238000002360 preparation method Methods 0.000 description 23
239000000243 solution Substances 0.000 description 21
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 14
235000019441 ethanol Nutrition 0.000 description 14
239000002585 base Substances 0.000 description 13
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
239000000047 product Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 9
102000000588 Interleukin-2 Human genes 0.000 description 9
108010002350 Interleukin-2 Proteins 0.000 description 9
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
210000001744 T-lymphocyte Anatomy 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
239000010410 layer Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
239000007787 solid Substances 0.000 description 7
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000005711 Benzoic acid Substances 0.000 description 6
125000000041 C6-C10 aryl group Chemical group 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
239000000443 aerosol Substances 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
235000010233 benzoic acid Nutrition 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 6
230000001419 dependent effect Effects 0.000 description 6
239000000651 prodrug Substances 0.000 description 6
229940002612 prodrug Drugs 0.000 description 6
230000035755 proliferation Effects 0.000 description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
125000004391 aryl sulfonyl group Chemical group 0.000 description 5
125000004404 heteroalkyl group Chemical group 0.000 description 5
231100000252 nontoxic Toxicity 0.000 description 5
230000003000 nontoxic effect Effects 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 4
229930105110 Cyclosporin A Natural products 0.000 description 4
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 4
108010036949 Cyclosporine Proteins 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 4
150000001447 alkali salts Chemical class 0.000 description 4
125000004657 aryl sulfonyl amino group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
229960001265 ciclosporin Drugs 0.000 description 4
239000012039 electrophile Substances 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000003826 tablet Substances 0.000 description 4
229960001967 tacrolimus Drugs 0.000 description 4
QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
PNZXMIKHJXIPEK-UHFFFAOYSA-N Amide-Cyclohexanecarboxylic acid Natural products NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
125000000539 amino acid group Chemical group 0.000 description 3
150000007514 bases Chemical class 0.000 description 3
229940077388 benzenesulfonate Drugs 0.000 description 3
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
229940073608 benzyl chloride Drugs 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
FKNQCJSGGFJEIZ-UHFFFAOYSA-N gamma-methylpyridine Natural products CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000002609 medium Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
239000003880 polar aprotic solvent Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
238000012360 testing method Methods 0.000 description 3
WLTDBVJBSRJJRJ-UHFFFAOYSA-N (5-aminopyridin-2-yl)-morpholin-4-ylmethanone Chemical compound N1=CC(N)=CC=C1C(=O)N1CCOCC1 WLTDBVJBSRJJRJ-UHFFFAOYSA-N 0.000 description 2
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125000003226 pyrazolyl group Chemical group 0.000 description 1
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JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
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239000008109 sodium starch glycolate Substances 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
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229940095064 tartrate Drugs 0.000 description 1
RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 1
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UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
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210000001685 thyroid gland Anatomy 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
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241000701447 unidentified baculovirus Species 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Diabetes (AREA)
Hematology (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Physical Education & Sports Medicine (AREA)
Neurosurgery (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Epidemiology (AREA)
Endocrinology (AREA)
Obesity (AREA)
Cardiology (AREA)
Dermatology (AREA)
Heart & Thoracic Surgery (AREA)
Pulmonology (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (AREA)
Oncology (AREA)
Pain & Pain Management (AREA)
Emergency Medicine (AREA)
Transplantation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

EA200201096A 2000-06-26 2001-06-05 СОЕДИНЕНИЯ ПИРРОЛО[2,3-d]ПИРИМИДИНА В КАЧЕСТВЕ ИММУНОДЕПРЕССАНТОВ EA006153B1 (ru)

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US21428700P	2000-06-26	2000-06-26
PCT/IB2001/000975 WO2002000661A1 (en)	2000-06-26	2001-06-05	PYRROLO[2,3-d]PYRIMIDINE COMPOUNDS AS IMMUNOSUPPRESSIVE AGENTS

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EA006153B1 true EA006153B1 (ru)	2005-10-27

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EP (2)	EP1686130B1 (et)
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BRPI0610278A2 (pt)	2005-05-13	2010-06-08	Irm Llc	compostos e composições como inibidores de proteìna cinase
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Also Published As

Publication number	Publication date
KR100516419B1 (ko)	2005-09-23
IL152771A0 (en)	2003-06-24
TNSN01095A1 (fr)	2005-11-10
ES2318605T3 (es)	2009-05-01
CZ20023993A3 (cs)	2004-02-18
HK1054930A1 (en)	2003-12-19
NO324934B1 (no)	2008-01-07
PT1294724E (pt)	2006-07-31
EP1294724A1 (en)	2003-03-26
SV2002000506A (es)	2002-10-24
US7192963B2 (en)	2007-03-20
US20030220353A1 (en)	2003-11-27
EP1294724B1 (en)	2006-04-19
AU784297B2 (en)	2006-03-02
US20020068746A1 (en)	2002-06-06
IL152771A (en)	2009-06-15
JP2004501922A (ja)	2004-01-22
MY127236A (en)	2006-11-30
GEP20053541B (en)	2005-06-10
DZ3359A1 (fr)	2002-01-03
HRP20021000A2 (en)	2005-02-28
HUP0301114A2 (hu)	2003-08-28
CA2412560C (en)	2008-12-30
CA2412560A1 (en)	2002-01-03
SI1294724T1 (sl)	2006-08-31
UA74370C2 (uk)	2005-12-15
PL359563A1 (en)	2004-08-23
CU23263B7 (es)	2008-03-14
DOP2001000200A (es)	2003-02-15
AR029279A1 (es)	2003-06-18
ECSP014105A (es)	2002-01-25
AP2002002695A0 (en)	2002-12-31
DE60118917T2 (de)	2006-11-30
BR0111561A (pt)	2003-09-09
AU6053801A (en)	2002-01-08
ATE323704T1 (de)	2006-05-15
SK17342002A3 (sk)	2004-06-08
NZ522364A (en)	2004-09-24
EE200200711A (et)	2004-06-15
DK1686130T3 (da)	2009-04-06
US6962993B2 (en)	2005-11-08
CN1439010A (zh)	2003-08-27
GT200100117A (es)	2002-01-31
MXPA03000068A (es)	2003-09-25
KR20030017561A (ko)	2003-03-03
US20070161666A1 (en)	2007-07-12
US6696567B2 (en)	2004-02-24
HUP0301114A3 (en)	2004-11-29
ZA200210275B (en)	2003-12-19
OA12292A (en)	2003-11-11
IS2305B (is)	2007-10-15
YU83302A (sh)	2005-09-19
ES2257410T3 (es)	2006-08-01
DE60118917D1 (de)	2006-05-24
AP1911A (en)	2008-10-30
TWI243820B (en)	2005-11-21
CN100351253C (zh)	2007-11-28
NO20026030D0 (no)	2002-12-16
US20050197349A1 (en)	2005-09-08
WO2002000661A1 (en)	2002-01-03
PA8521101A1 (es)	2002-04-25
EP1686130B1 (en)	2009-02-18
BG107236A (bg)	2003-09-30
NO20026030L (no)	2002-12-16
MA26917A1 (fr)	2004-12-20
DE60137734D1 (de)	2009-04-02
JP4068958B2 (ja)	2008-03-26
PE20020381A1 (es)	2002-05-13
IS6606A (is)	2002-10-31
AU784297C (en)	2007-01-11
ATE423120T1 (de)	2009-03-15
EP1686130A1 (en)	2006-08-02
EA200201096A1 (ru)	2003-04-24
DK1294724T3 (da)	2006-07-17

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